ethyl ((2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl (2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl phosphate

ID: ALA3608397

Cas Number: 35002-96-1

PubChem CID: 3081472

Max Phase: Preclinical

Molecular Formula: C22H31N4O12P

Molecular Weight: 574.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OC[C@H]1O[C@@H](n2cc(C)c(=O)[nH]c2=O)C[C@@H]1O)O[C@H]1C[C@H](n2cc(C)c(=O)[nH]c2=O)O[C@@H]1CO

Standard InChI:  InChI=1S/C22H31N4O12P/c1-4-34-39(33,35-10-16-13(28)5-17(37-16)25-7-11(2)19(29)23-21(25)31)38-14-6-18(36-15(14)9-27)26-8-12(3)20(30)24-22(26)32/h7-8,13-18,27-28H,4-6,9-10H2,1-3H3,(H,23,29,31)(H,24,30,32)/t13-,14-,15+,16+,17+,18+,39?/m0/s1

Standard InChI Key:  ZKKPILTYCWGWSA-KJOYEBRGSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3608397

   Dtpdt ethylphosphotriester

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 574.48

Molecular Weight (Monoisotopic): 574.1676

AlogP: -0.82

#Rotatable Bonds: 10

Polar Surface Area: 213.40

Molecular Species: NEUTRAL

HBA: 14

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.66

CX Basic pKa: ┄

CX LogP: -0.73

CX LogD: -0.73

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.26

Np Likeness Score: 0.61

References

1. Hayashi J, Hamada T, Sasaki I, Nakagawa O, Wada S, Urata H..  (2015)  Synthesis of novel cationic spermine-conjugated phosphotriester oligonucleotide for improvement of cell membrane permeability.,  25  (17): [PMID:26149182] [10.1016/j.bmcl.2015.06.071]

Source

Source(1):

• Scientific Literature